JP3984280B1 - 化学修飾フラーレンおよびその製造方法,化学修飾フラーレンを含有するプロトン伝導膜 - Google Patents
化学修飾フラーレンおよびその製造方法,化学修飾フラーレンを含有するプロトン伝導膜 Download PDFInfo
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 239000012528 membrane Substances 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 15
- 239000003792 electrolyte Substances 0.000 claims abstract description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 13
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 9
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910012258 LiPO Inorganic materials 0.000 claims abstract description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 7
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 6
- 229910003472 fullerene Inorganic materials 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 13
- 229910021645 metal ion Inorganic materials 0.000 claims description 7
- -1 platinum ion Chemical class 0.000 claims description 6
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910001424 calcium ion Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000007336 electrophilic substitution reaction Methods 0.000 abstract description 4
- 239000000446 fuel Substances 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000000862 absorption spectrum Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920000557 Nafion® Polymers 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009841 combustion method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000005518 polymer electrolyte Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 125000001918 phosphonic acid ester group Chemical group 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/122—Ionic conductors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2604/00—Fullerenes, e.g. C60 buckminsterfullerene or C70
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/932—Specified use of nanostructure for electronic or optoelectronic application
- Y10S977/948—Energy storage/generating using nanostructure, e.g. fuel cell, battery
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- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Carbon And Carbon Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Conductive Materials (AREA)
Abstract
【解決手段】 スルホン酸基SO3Mおよび/またはホスホン酸基PO(OM)2(MはHまたはアルカリ金属イオン)が直接結合し、有機化合物が実質的に結合していないプロトン伝導膜電解質用の化学修飾フラーレン、および、スルホン化試薬K2SO3の場合は(ジメチルアセトアミド+水)、ホスホン化試薬LiPO(OEt)2の場合はジオキサンという特定の反応溶媒を用いる該化学修飾フラーレンの製造方法。
【選択図】 なし
Description
また、上記の化学修飾フラーレンが含まれたプロトン伝導膜も本発明であり、ホスホン
酸基が、カルシウムイオンや白金イオンなどの多価金属イオンにより金属イオン架橋されたプロトン伝導膜も本発明である。
ここに亜硫酸カリウムK2SO3 790mg(フラーレンの5倍モル)を水10mlに溶かして添加した後、80℃で4日間加熱撹拌した。反応終了後、溶媒を乾燥除去して残渣をエタノールで抽出した。固形分を濾別し、濾液のエタノールを乾燥除去した後、赤外吸収スペクトルをKBrを用いて測定したところ、1117cm−1にSO2伸縮、619cm−1にCS伸縮のピークが表れた(図1参照)。また、ICP−AES(誘導結合プラズマ原子発光スペクトル法)によりS、K分析を行い、燃焼法でC、H、Oの元素分析を行った結果は、C57.5%、S11.4%、K14.7%、H0.55%、O13.0%であり、スルホン酸基SO3KとHが4〜5個程度結合していることが確認された。更に、試料をD2Oに溶解してNMRを測定したところ、ベータ位のプロトンと推定されるピークが確認された。得られたスルホン酸化フラーレンの収率は、フラーレンベースでおよそ30%であった。
実施例1において、ジメチルアセトアミドの代わりにジメチルホルムアミドを用いて同様に操作し、生成物の赤外吸収スペクトルを測定したところ、多くのピークが表れ、溶媒のジメチルホルムアミドが結合していることが確認された(図2参照)。
これに塩化カルシウム10mgを水5mlに溶かした溶液を加えてホモジナイザーで30分間撹拌した。得られた分散液を、100ミクロンのガラス繊維不織布(日本バイリーン社製)上に刷毛を用いて塗布し、間隙に含浸させた。この操作を10回繰り返した後、100℃で乾燥させてプロトン伝導膜を得た。該膜を水に一晩浸漬し、ICP−AESを用いてP分析値の変化を測定したが浸漬前後で差はなく、ホスホン酸化フラーレンは溶出していないことが確認された。
Claims (4)
- スルホン化試薬K2SO3の場合は(ジメチルアセトアミド+水)、ホスホン化試薬LiPO(OEt)2の場合はジオキサンという特定の反応溶媒を選択し、該溶媒中にフラーレンとK 2 SO 3 またはLiPO(OEt) 2 とを分散させ、常圧または加圧下で、20−200℃の反応温度を用いて、10−200時間反応させる請求項1に記載の化学修飾フラーレンの製造方法。
- 請求項1記載の化学修飾フラーレンを含有したプロトン伝導膜。
- ホスホン酸基が、カルシウムイオンや白金イオンなどの多価金属イオンにより金属イオン架橋された請求項3記載のプロトン伝導膜。
Priority Applications (3)
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JP2006323201A JP3984280B1 (ja) | 2006-11-30 | 2006-11-30 | 化学修飾フラーレンおよびその製造方法,化学修飾フラーレンを含有するプロトン伝導膜 |
PCT/JP2007/073084 WO2008066126A1 (fr) | 2006-11-30 | 2007-11-29 | Fullerène chimiquement modifié, son procédé de production et film conducteur de protons comprenant du fullerène chimiquement modifié |
US12/453,802 US8088534B2 (en) | 2006-11-30 | 2009-05-22 | Chemically modified fullerene, production method for the same, and proton conducting membrane including the same |
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JP2006323201A JP3984280B1 (ja) | 2006-11-30 | 2006-11-30 | 化学修飾フラーレンおよびその製造方法,化学修飾フラーレンを含有するプロトン伝導膜 |
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JP2008137905A JP2008137905A (ja) | 2008-06-19 |
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WO (1) | WO2008066126A1 (ja) |
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US8088534B2 (en) | 2006-11-30 | 2012-01-03 | Science Laboratories, Inc. | Chemically modified fullerene, production method for the same, and proton conducting membrane including the same |
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JP5635282B2 (ja) | 2010-03-15 | 2014-12-03 | ソニー株式会社 | 判別装置 |
JP5719159B2 (ja) | 2010-03-15 | 2015-05-13 | ソニー株式会社 | 評価装置 |
JP5736116B2 (ja) | 2010-03-15 | 2015-06-17 | ソニー株式会社 | 算出装置 |
JP2012147937A (ja) | 2011-01-19 | 2012-08-09 | Sony Corp | レーザ治療装置、レーザ治療システム及び判別方法 |
US9959949B2 (en) | 2013-06-04 | 2018-05-01 | Savannah River Nuclear Solutions, Llc | Solid state electrolyte composites based on complex hydrides and metal doped fullerenes/fulleranes for batteries and electrochemical applications |
CN104466244B (zh) * | 2013-09-12 | 2017-12-22 | 华为技术有限公司 | 一种非水有机高电压电解液添加剂、非水有机高电压电解液和锂离子二次电池 |
WO2021150256A1 (en) * | 2020-01-26 | 2021-07-29 | Butzloff Peter Robert | Fullerene phosphonates, method, and medicament |
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JP4715023B2 (ja) * | 2001-05-08 | 2011-07-06 | ソニー株式会社 | フラーレン誘導体の製造方法 |
JP4333085B2 (ja) | 2002-02-05 | 2009-09-16 | ソニー株式会社 | プロトン伝導体及びその製造方法、プロトン伝導性高分子及びその製造方法、並びに電気化学装置 |
US6890676B2 (en) * | 2002-02-05 | 2005-05-10 | Sony Corporation | Fullerene based proton conductive materials |
CA2529013A1 (en) * | 2003-06-12 | 2004-12-23 | Materials And Electrochemical Research (Mer) Corporation | Fullerene-based electrolyte for fuel cells |
JP4320581B2 (ja) * | 2003-08-04 | 2009-08-26 | ソニー株式会社 | イオン伝導体、並びに電気化学装置 |
JP4524579B2 (ja) | 2003-08-08 | 2010-08-18 | ソニー株式会社 | プロトン伝導性複合体並びに電気化学デバイス |
JP4351557B2 (ja) | 2004-03-03 | 2009-10-28 | 本田技研工業株式会社 | プロトン伝導体 |
JP3984280B1 (ja) | 2006-11-30 | 2007-10-03 | 株式会社サイエンスラボラトリーズ | 化学修飾フラーレンおよびその製造方法,化学修飾フラーレンを含有するプロトン伝導膜 |
-
2006
- 2006-11-30 JP JP2006323201A patent/JP3984280B1/ja not_active Expired - Fee Related
-
2007
- 2007-11-29 WO PCT/JP2007/073084 patent/WO2008066126A1/ja active Application Filing
-
2009
- 2009-05-22 US US12/453,802 patent/US8088534B2/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8088534B2 (en) | 2006-11-30 | 2012-01-03 | Science Laboratories, Inc. | Chemically modified fullerene, production method for the same, and proton conducting membrane including the same |
Also Published As
Publication number | Publication date |
---|---|
US8088534B2 (en) | 2012-01-03 |
US20090297914A1 (en) | 2009-12-03 |
WO2008066126A1 (fr) | 2008-06-05 |
JP2008137905A (ja) | 2008-06-19 |
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